Ok, so since I am heading to Gencon this year, how tough is it to update my SR4 Hacker to SR5? Is there a simple way of doing it, or am I better off just starting from scratch and hoping Hero Labs has SR5 ready before Gencon?

Assuming that you're playing Missions, you can't really update him. Check out the Season 5 Missions FAQ for rules to change your SR4 Missions character into an SR5 Prime Runner so you can sign up for the vaporware Prime Runner missions. You're better off making a new SR5 decker that maintains the theme of the previous character.

Excellent that is what I needed to know. Thanks!

Hero Lab for Shadowrun 5th edition should be released the 23rd of may this year.